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Lil Wayne

Why we underestimated him: We didn't think he'd have much of a career after Cash Money fell apart and we definitely didn't think he'd eventually become the Best Rapper Alive.

When he proved us wrong: When he dropped his 2004 album, Tha Carter, and then followed it up by going on an absolute tear on the mixtape circuit over the next five years.

Prior to Tha Carter, Wayne had scored a handful of hits both on his own and as a member of Cash Money's Hot Boys. We thought he was cool, but no one thought he was on his way to becoming the beast he eventually became. Wayne took things to another level in 2004 by releasing the first of eight consecutive albums to land on top of the Billboard Rap Albums chart.

He has sold more than 15 million albums during his career, scored dozens and dozens of Top 40 hits, and many of his mixtapes—including 2006's Dedication 2, 2007's Da Drought 3, and 2009's No Ceilings—are considered classics in their own right. All that for a guy we once thought would never contribute anything more to hip-hop besides the phrases "bling bling" and "drop it like it's hot."